HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Isle of Wight

$211+ Cheap flights from Portland, ME (PWM) to Isle of Wight, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — RIC
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Isle of Wight with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Isle of Wight are usually found in May or August, booked 46 days in advance, depart on a Monday or Friday and return on a Tuesday

Cheap flight deals from Portland to Isle of Wight

Cheapest flights from Portland to Isle of Wight
Explore the most affordable flight options available from Portland to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:30 pmPWM - ORF
1 stop4h 11mUnited Airlines
Tue 1/610:39 amORF - PWM
1 stop3h 52mUnited Airlines
Deal found 12/16$275
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:00 amPWM - ORF
1 stop4h 59mUnited Airlines
Tue 1/610:39 amORF - PWM
1 stop3h 52mUnited Airlines
Deal found 12/16$352
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:01 pmPWM - ORF
1 stop4h 21mUnited Airlines
Sun 1/410:46 amORF - PWM
1 stop3h 54mUnited Airlines
Deal found 12/16$370
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:16 amPWM - ORF
2 stops26h 50mMultiple Airlines
Tue 1/67:40 pmORF - PWM
1 stop14h 42mMultiple Airlines
Deal found 12/16$415
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:46 pmPWM - ORF
1 stop4h 33mUnited Airlines
Wed 12/317:55 pmORF - PWM
1 stop4h 04mUnited Airlines
Deal found 12/17$435
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:30 pmPWM - ORF
1 stop6h 05mSouthwest
Tue 1/68:50 amORF - PWM
1 stop3h 20mSouthwest
Deal found 12/16$459
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:15 amPWM - ORF
1 stop5h 18mDelta
Thu 12/253:45 pmORF - PWM
1 stop6h 58mDelta
Deal found 12/17$490
This Kiwi.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/199:46 amPWM - ORF
1 stop28h 20mMultiple Airlines
Thu 12/2512:38 pmORF - PWM
2 stops20h 28mMultiple Airlines
Deal found 12/17$543
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:39 amPWM - ORF
1 stop4h 03mAmerican Airlines
Wed 12/316:07 pmORF - PWM
1 stop4h 44mAmerican Airlines
Deal found 12/17$568

Find flight deals from Portland to Isle of Wight

Keep the following information in mind while searching for Portland to Isle of Wight flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$124
(Breeze Airways)

Popular in

December

Cheapest in

May

Average price

$429
Provider with most accurate pricing for Boston Logan Intl-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Norfolk flights.
Search Deals
From Portland to Isle of Wight
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Isle of Wight that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Portland to Isle of Wight that are best for you.

Fly from

Portland

Fly to

Isle of Wight

Route

Depart

Return

Price

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Fri 1/23

9:47 am-9:50 pm

1 stop12h 03m

Norfolk

Thu 1/29

6:45 am-9:07 am

1 stop26h 22m

$311

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 3/25

6:25 am-11:50 am

1 stop5h 25m

Norfolk

Mon 3/30

5:18 pm-12:10 am

1 stop6h 52m

$342

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 4/8

6:10 am-3:50 pm

2 stops9h 40m

Norfolk

Mon 4/13

10:05 am-2:10 pm

1 stop4h 05m

$347

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 5/6

3:15 pm-11:39 pm

2 stops8h 24m

Norfolk

Sat 5/9

6:08 am-10:24 am

1 stop4h 16m

$347

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Mon 2/23

3:55 pm-10:10 pm

1 stop6h 15m

Norfolk

Fri 2/27

11:25 am-4:15 pm

1 stop4h 50m

$350

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Tue 12/30

6:00 am-10:59 am

1 stop4h 59m

Norfolk

Tue 1/6

10:39 am-2:31 pm

1 stop3h 52m

$352

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 3/25

5:30 am-5:50 pm

2 stops12h 20m

Norfolk

Mon 3/30

6:20 am-4:50 pm

2 stops10h 30m

$352

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Fri 1/23

5:45 am-4:45 pm

2 stops11h 00m

Norfolk

Thu 1/29

10:20 am-10:15 pm

2 stops11h 55m

$360

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Thu 3/26

5:30 am-12:35 pm

1 stop7h 05m

Norfolk

Mon 3/30

5:18 pm-12:10 am

1 stop6h 52m

$367

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Thu 4/30

4:50 pm-11:33 pm

1 stop6h 43m

Norfolk

Sun 5/3

5:50 am-11:55 am

1 stop6h 05m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 13 results
1
2

Best time to book a flight from Portland to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Isle of Wight

How far ahead should I book a flight from Portland, Maine to Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Isle of Wight. Price data was last updated on December 12, 2025.

The price you pay for your flight from Portland, Maine to Isle of Wight may vary depending on when you book. For the best chance of a lower fare, look to book 11 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Portland, Maine to Isle of Wight?

Currently, July is the cheapest month in which you can book a flight from Portland, Maine to Isle of Wight (average of $52). Flying from Portland, Maine to Isle of Wight in September is currently the most expensive (average of $108). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PWM to I1W?

Find hourly flight availability from Portland to Isle of Wight. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

One of the essential ways to save on airfare from Portland, Maine to Isle of Wight is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 40% on airfare.

What is the cheapest day to fly from Portland, Maine to Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from Portland to Isle of Wight. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland, Maine to Isle of Wight flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated December 18, 2025.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, and Delta from Portland to Isle of Wight to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Entertainment

6.7

Comfort

8.2

Crew

8.8

Overall

8.2

Boarding

8.4

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
248 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Entertainment

6.7

Comfort

8.2

Crew

8.8

Overall

8.2

Boarding

8.4

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Southwest
7.9
Good
4,250 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Entertainment

6.7

Comfort

8.2

Crew

8.8

Overall

8.2

Boarding

8.4

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Delta
7.9
Good
8,008 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Entertainment

6.7

Comfort

8.2

Crew

8.8

Overall

8.2

Boarding

8.4

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
United Airlines
7.4
Good
9,093 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Entertainment

6.7

Comfort

8.2

Crew

8.8

Overall

8.2

Boarding

8.4

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,055 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Entertainment

6.7

Comfort

8.2

Crew

8.8

Overall

8.2

Boarding

8.4

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

Related info for your journey

Find useful and relevant information for your journey from Portland to Isle of Wight. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Isle of Wight?

    For a flight from Portland to Isle of Wight, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 outbound flights to Isle of Wight per day. 5 airlines have flights to Isle of Wight from Portland on a regular basis.

  • How long is the flight from Portland, Maine to Isle of Wight?

    A quick flight from Portland, Maine to Isle of Wight can take about 5h 25m. Delta provides one of the quickest options available for as low as $342. Airlines will cover a distance of 560 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Portland, Maine to Isle of Wight one-way?

    One-way options have recently been found by users for as low as $61 on Breeze Airways. Other airlines that offer cheap prices include American Airlines from $99 and Southwest from $109 one-way.

  • Can I find deals for flights from Portland to Isle of Wight that include hotel bookings?

    Yes. In addition to deals on Portland to Isle of Wight flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Isle of Wight?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Isle of Wight.

  • Can I find deals for business class flights from Portland to Isle of Wight?

    Yes. Cheapflights offers flight deals from Portland to Isle of Wight by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Isle of Wight?

    Currently, July is the cheapest month in which you can book a flight from Portland, Maine to Isle of Wight (average of $52). Flying from Portland, Maine to Isle of Wight in September is currently the most expensive (average of $108). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Reagan-National flights
Boston to Dulles Intl flights
Boston to Raleigh flights
Boston to Richmond flights
Portland to Dulles Intl flights
Boston to Norfolk flights
Portland to Reagan-National flights
Boston to Greensboro flights
Boston to Charlottesville flights
Portland to Norfolk flights
Bangor to Norfolk flights
Bangor to Richmond flights
Bangor to Reagan-National flights
Boston to Roanoke flights
Bangor to Dulles Intl flights
Portland to Raleigh flights
Portland to Richmond flights
Bangor to Raleigh flights
Boston to Blountville flights
Boston to Newport News flights
Portland to Greensboro flights
Boston to Lynchburg flights
Boston to Salisbury flights
Portland to Charlottesville flights
Bar Harbor to Reagan-National flights
Bangor to Charlottesville flights
Augusta to Reagan-National flights
Portland to Roanoke flights
Augusta to Raleigh flights
Rockland to Raleigh flights
Portland to Newport News flights
Boston to Staunton flights
Boston to Lewisburg flights
Portland to Staunton flights
Portland to Blountville flights
Bangor to Blountville flights
Rockland to Dulles Intl flights
Augusta to Dulles Intl flights

Top 5 airlines flying from Portland to Isle of Wight

Discover the top 5 airlines that operate flights from Portland to Isle of Wight. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$62Average$163FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$120Average$288FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$163Average$376FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$218Average$358FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$236Average$340FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.